Boron tribromide → HCID 22459064, compound

HRID 613413Notes

Reaction equation

HRID 613413 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18]C)=[CH:17][C:12]=3[S:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=3[S:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22458950HCID 22458950, compound

Product 1

HCID 22459064HCID 22459064, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred, -10° C. solution of the product from Step D (5.483 grams; dry methylene chloride; 60 mL) was treated with 1M boron tribromide solution (methylene chloride; 20.81 mL). After 2 hours, the reaction was momentarily warmed to ambient temperature. It was partitioned between isopropyl acetate and aqueous sodium bicarbonate, washed once with water and dried over magnesium sulfate. Filtration and evaporation produced a semi-solid. Chromatography over silica gel (2.5:1 hex/ethyl acetate) resulted in the isolation of the title compound, a pale yellow solid.

Workup

  1. customIt was partitioned between isopropyl acetate and aqueous sodium bicarbonate
  2. washwashed once with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and evaporation
  5. customproduced a semi-solid

Sources & evidence

ORD record
ord-f76a95c523a4467aabb1792095a6190d
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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